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S8692

Sigma-Aldrich

Sulprostone

≥95% (HPLC), oil

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Synonym(s):
(5Z,11α,13E,15R)--11,15-Dihydroxy-9-oxo-16-phenoxy-17,18,19,20-tetranorprosta-5,13-dienoic acid methane sulfonamide, CP-34089, SHB-286, ZK-57671
Empirical Formula (Hill Notation):
C23H31NO7S
CAS Number:
Molecular Weight:
465.56
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.77

assay

≥95% (HPLC)

form

oil

color

colorless to yellow-brown

solubility

DMSO: >10 mg/mL

shipped in

wet ice

storage temp.

−20°C

SMILES string

CS(=O)(=O)NC(=O)CCC\C=C/C[C@@H]1[C@@H](\C=C\[C@@H](O)COc2ccccc2)[C@H](O)CC1=O

InChI

1S/C23H31NO7S/c1-32(29,30)24-23(28)12-8-3-2-7-11-19-20(22(27)15-21(19)26)14-13-17(25)16-31-18-9-5-4-6-10-18/h2,4-7,9-10,13-14,17,19-20,22,25,27H,3,8,11-12,15-16H2,1H3,(H,24,28)/b7-2-,14-13+/t17-,19-,20-,22-/m1/s1

InChI key

UQZVCDCIMBLVNR-TWYODKAFSA-N

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1 of 4

This Item
P5515P5640P0424
vibrant-m

S8692

Sulprostone

vibrant-m

P5515

Prostaglandin E1

vibrant-m

P5640

Prostaglandin E2

vibrant-m

P0424

Prostaglandin F tris salt

Quality Level

100

Quality Level

200

Quality Level

200

Quality Level

200

assay

≥95% (HPLC)

assay

≥98% (HPLC)

assay

≥93% (HPLC)

assay

≥99%

shipped in

wet ice

shipped in

-

shipped in

ambient

shipped in

ambient

color

colorless to yellow-brown

color

-

color

-

color

white

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

storage temp.

−20°C

Application

Human chondrocytes3 and mouse adrenal chromaffin cells4 were treated with sulprostone to study the biological effects of PGE2.

Biochem/physiol Actions

Sulprostone is an analog of prostaglandin E2 (PGE2)1 and antagonizes vasopressin-induced antidiuretic responses in cells from rat renal inner medullae by a mechanism that involves activation of Rho.2
Selective EP3 prostanoid receptor agonist.

pictograms

Exclamation markHealth hazard

signalword

Danger

Hazard Classifications

Eye Irrit. 2 - Repr. 1B - Skin Irrit. 2 - STOT SE 3

target_organs

Respiratory system

Storage Class

6.1C - Combustible, acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type ABEK (EN14387) respirator filter


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Ioannis D Gallos et al.
The Cochrane database of systematic reviews, 4, CD011689-CD011689 (2018-04-26)
Postpartum haemorrhage (PPH) is the leading cause of maternal mortality worldwide. Prophylactic uterotonic drugs can prevent PPH, and are routinely recommended. There are several uterotonic drugs for preventing PPH but it is still debatable which drug is best. To identify
Xin Li et al.
Arthritis and rheumatism, 60(2), 513-523 (2009-01-31)
To elucidate the pathophysiologic links between prostaglandin E(2) (PGE(2)) and osteoarthritis (OA) by characterizing the catabolic effects of PGE(2) and its unique receptors in human adult articular chondrocytes. Human adult articular chondrocytes were cultured in monolayer or alginate beads with
W Ma et al.
European journal of pain (London, England), 22(5), 845-861 (2018-01-18)
Prostaglandin E2 (PGE2) enriched in inflamed tissues contributes to chronic pain by sensitizing nociceptive dorsal root ganglion (DRG) neurons (nociceptors). Of four PGE2 receptors (EP1-4), EP4 plays a major role in PGE2-induced nociceptor sensitization. We have previously reported that PGE2
Koen Van Crombruggen et al.
Naunyn-Schmiedeberg's archives of pharmacology, 383(6), 613-626 (2011-04-28)
Extensively based on evidence gained from experimental animal models, the transient receptor potential vanilloid receptor type 1 (TRPV1)-activator capsaicin is regarded as a valuable tool in the research on neurogenic inflammation. Although capsaicin-related drugs gained renewed interest as a therapeutic
Keith Morrison et al.
The Journal of pharmacology and experimental therapeutics, 365(3), 727-733 (2018-03-29)
Selexipag [2-{4-[(5,6-diphenylpyrazin-2-yl)(isopropyl)amino]butoxy}-N-(methylsulfonyl)acetamide] is a selective nonprostanoid prostacyclin (PGI2) receptor (IP receptor) agonist that is approved for the treatment of pulmonary arterial hypertension (PAH). In contrast to selexipag, PGI2 analogs used in the clinic are nonselective agonists at prostanoid receptors and

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